Winter Timeshare Rentals
Winter getaways are always popular, making now the perfect time to secure exclusive timeshare deals for your seasonal escape! Whether you're dreaming of a snowy mountain retreat or a warm-weather getaway, these timeshare rentals offer the perfect setting to make your winter vacation unforgettable.
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,099 ($728/night)
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Club Wyndham Nashville
Nashville, Tennessee- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,057 ($151/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
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Novaispania Residences by Pueblo Bonito
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 4 bed/4.5 bath, sleeps 12
- $9,071 ($1,296/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,977 ($711/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,848 ($407/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,609 ($1,230/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,230 ($461/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–5, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $901 ($300/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–5, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $901 ($300/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,916 ($559/night)
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Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Jan 2–7, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,284 ($657/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,403 ($486/night)
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Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $746 ($107/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,800 ($1,257/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,031 ($576/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,091 ($870/night)
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Marriott's Grande Vista
Orlando, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($673/night)
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Grand Solmar Pacific Dunes Resort Golf & Spa
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $3,649 ($521/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 2–9, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $8,838 ($1,263/night)
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Club Wyndham Santa Barbara
Pompano Beach, Florida- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $1,358 ($194/night)
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The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,963 ($1,280/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,930 ($704/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,099 ($728/night)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,469 ($496/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,764 ($1,109/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $1,660 ($237/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($412/night)
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The Galleon Resort
Key West, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,464 ($1,066/night)
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Villa La Estancia Cabo San Lucas
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 3 bed/4 bath, sleeps 8
- $8,745 ($1,249/night)
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,141 ($228/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 2–6, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $897 ($224/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $4,271 ($610/night)
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Villa del Palmar Cabo San Lucas
Cabo San Lucas, Mexico- Jan 2–9, 2027 (7 nights)
- 3 bed/3 bath, sleeps 6
- $6,892 ($985/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 2–6, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $940 ($235/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,916 ($559/night)
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Villa del Palmar Vallarta
Puerto Vallarta, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $4,330 ($619/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
Royal Haciendas
Playa del Carmen, Mexico- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,428 ($347/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,580 ($797/night)
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The Point at Poipu
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,599 ($657/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,748 ($821/night)